Holiday rentals with a patio in Ocean Pines

Gorgeous New Beachfront! King Bed, Direct Sea View

Stunning beachfront condo with direct view of the ocean! Your vacation home away from home! Everything you need right ON the beach. All linens, supplies and a well-stocked kitchen! New 65" TV w/free 4K Netflix provided! Modern serene decor in the heart of OC! Feel like getting out? Enjoy walking distance to Seacrets, Mackey's, and Fager's Island, Subway, Candy Kitchen or Dumsers' Dairyland! More adventure? Walk to minigolf, pontoon boats and jetski rentals! Only 4 minute drive to the boardwalk!!

Whimsical Willow w/ Beach Club Pass and No Pet Fee

Discover this charming 3-bedroom home! With wood floors throughout, it features a king master suite, a queen bedroom, and a kids’ room with a twin-over-full bunk. Enjoy a fully stocked kitchen, fast WiFi, a screened-in porch, and a jetted tub for ultimate relaxation. Perfect for families or dual-family stays! Explore Ocean Pines or take a quick 10-minute drive to Ocean City for endless fun. Included is the Beach Club Parking Pass! Plus- A local manager is here to ensure everything goes smoothly.

Salty Serenity

Relax and recharge at our cozy 3 bed/2 bath home in Ocean Pines, a peaceful community near Ocean City, MD. Enjoy bikes, kayaks, and a fire pit in the large backyard, or use the pools, marina, yacht club, and golf course in the neighborhood. Beach parking at the Ocean Pines Beach Club in Ocean City is included. You can explore the boardwalk, casino, outlets, and the many nearby restaurants. Or, visit Berlin, or see the wild horses at Assateague Island. Come experience all the area has to offer!

The Whale’s Tale Retreat w/ Beach Club Pass

Welcome to your charming home away from home in beautiful Ocean Pines, MD. Located on a large corner lot in a peaceful community but close to all the action. It’s the perfect blend of beachy fun and laid-back comfort. The Space • Bright & comfortable living area for movie nights or game time • Loft hallway that overlooks the living room, adding an open and airy feel • Screened-in porch for morning coffee or evening cocktails bug-free • Fire pit + tiki torches to set the perfect vacation mood

For 5(28)

Your family will be close to everything when you stay at this centrally-located home. We are 10-15 minutes to OC beaches, historic Berlin, and 30 min. to Del. beaches and Assategue Island with it's wild ponies. And minutes to the Ocean Pines amenities; 5 pools, beach access, golf course, racket sports, bike, walk paths and nightly live entertainment. Then come back to the quiet home where you have plenty of room to stretch out inside or outside. Quiet back yard porch, patio, and bbq grill.

OC Gateway: Modern 4BR/2.5BA home (dog friendly)

Have fun with the whole family at our stylish Ocean City-convenient home! This wooded beach house boasts many modern upgrades including a beautiful kitchen with gas range, large flat panel televisions in almost every room, a washer and dryer, and even a Wii video game system in the living room! Queens in 3 bedrooms and a bunk bed with trundle in the 4th! Finally, enjoy all the amenities of Ocean Pines including access to 5 pools, a private OC beach club (w/pool!), and much more! Lic. No. 4586

Ocean Pines Fun – Arcade, Pools & Near O.C. Beach

Unwind at our peaceful, family-friendly retreat nestled in the trees of Ocean Pines, MD. This serene home sleeps 8 and offers the perfect blend of quiet relaxation and coastal fun. Enjoy easy access to seasonal community pools and amenities, Ocean City beaches (under 10 miles), Ocean Pines Golf Club (2 miles), historic Berlin, and Assateague’s wild horses. Kids love the arcade system, nearby playgrounds, trails, and restaurants. Book your stay and follow us on IG @OceanPinesVacation.

Studio Charm w/ Deck: Walk to Beach & Dining!

This charming OC studio promises nothing but good vibes! The studio has a full bath, an open layout with an electric fireplace, a fully equipped kitchen, and washer and dryer. Relax on the private balcony, sipping a drink in a hanging chair or dining at the patio table. Proximity to Jolly Roger Amusement Park and Splash Mountain Water Park adds to the excitement, while numerous restaurants and shops are a short stroll away. The beach and boardwalk are just a few blocks from your doorstep!

Beautiful Spacious 4 Bedroom Home in Ocean Pines

This 4 bedroom 3 1/2 bath home features a full kitchen, dishwasher, microwave, washer, dryer, 5 TVs, fireplace, outdoor grill, outdoor shower, screened porch and much more. Located in Ocean Pines on the golf course at hole #6, just minutes from Ocean City. This is a family friendly community offering many amenities (golf, Yacht Club, playgrounds, pools, tennis courts, basketball courts, walking trails, and more!) Enjoy free parking pass to the Beach Club in Ocean City on 49th street.

Updated 3 Bedroom 2 Bathroom Home - Ocean Pines

Beautifully updated and recently renovated, rancher on a great street in Ocean Pines perfect for families and adults looking for a relaxing stay. We offer 3 bedrooms and 2 bathrooms on one level, with new large flat screen TV's, stainless appliances, and everything you'll need for your stay. We have a large driveway and a screened patio. Ocean Pines boasts over a dozen parks and walking trails, a public Yacht Club, 5 pools, 2 marinas, and a championship golf course - 10 min to the beach!

Cozy beach home away from home!

Welcome! Come enjoy a cozy experience at this centrally located home in the desired Ocean Pines Community! This home is near the playground and allows access to the on-site golf course, five pools (including indoor pool!) tennis courts, and marina for a small fee. Fun in the sun awaits 15 minutes away in downtown Ocean City, where you can stroll the boardwalk, lounge on the sand, or hit the amusement park. Plenty of restaurants, grocery stores and shopping within 15 minutes.

Hobbs & Rose | A Peaceful Cottage Escape

Built in 1941 from historic “clinker bricks,” this restored cottage is a dreamy place to slow down and reconnect. Surrounded by enchanted gardens and close to the beach, Hobbs & Rose is filled with charm—gorgeous living spaces, a carved marble soaking tub, and thoughtful details throughout. Enjoy a romantic getaway and unwind in our Sanctuary meditation room, where birdsong and forest friends welcome you. You relax—we’ve created every detail to help you feel restored.